Trying to make a living in rock 'n' roll (or hip-hop or R&B or pop) is a long-shot at best. But a career in jazz is not for the faint of heart.

Beside the unavoidable realities of fewer venues in which to ply your art, fewer labels to promote your recordings, and a smaller audience to support your efforts, there is also something of an institutional stodginess when it comes to newcomers. For a music genre renowned for the improvisational abilities of its artists, jazz can often be overly steeped in tradition. Perhaps because its most famous players are considered to be towering musical geniuses—particularly mid-century masters like Monk, Davis, Mingus—up-and-coming performers find it difficult to step out from their shadows.

Meanwhile, many fans pledge their allegiance to particular styles of jazz, uncomfortable with hopping the (unnecessary) dividing lines between hard bop and fusion or even (yikes!) "soft."

But Brad Mehldau has led a charmed career, mostly avoiding restrictive typecasting or comparisons to legends. He's managed to forge his own particular style that appeals to traditionalists and neu jazz fans alike, traversing sub-genres from straight-ahead jazz to orchestral pieces to prog electronica. The 44-year-old pianist is undoubtedly one of the leading artists in contemporary jazz—just as some music writers predicted when he first hit as a band leader in the mid '90s and signed with Warner Bros. Records. His ensuing The Art of the Trio series of albums (with bassist Larry Grenadier and drummer Jorge Rossy) revealed a pianist steeped in the nuances of his forebears—from, say, Bill Evans' gentle melancholy to Wynton Kelly's melodic joy, not to mention Herbie Hancock's pure catchiness—but not chained to them. He was able to establish an inviting, expressive sound that calls to mind classic trios without sounding old-fashioned (unlike some of the "young lions" of the 1980s jazz scene).

His knack for clear-eyed reverence developed at the New School, where he studied jazz. But even before he became a journeyman player gigging with famous musicians like drummer Jimmy Cobb or saxophonist Joshua Redman, he wanted to get the classic repertoire down. It was a perfectly practical matter—he wanted to do a good job.

"I wanted to be able to know those songs, as many as possible, so as to not be stumped in a gig situation," he writes in an e-mail interview. "Some of my first gigs were with singers while I was still in high school, where he or she might say, ‘Okay, let's do "The More I See You" in B flat,' and then just start counting off a tempo, expecting the pianist to make an introduction. So it was more a necessity, like how a taxi driver should know every street in a city."

Making the transition from competent cover musician to inspired artist can be a torturous journey full of mental traps—can you really come up with new, melodious sounds that can even compare to those classic songs you've memorized? But Mehldau says he did not particularly worry about sounding too much like legendary pianists, or ponder how to differentiate himself from them. Instead, his ear was attuned to the interplay of great jazz bands as a whole—that's the feel he wanted to create.

"I never focused on piano in particular," he says. "I would say that, just as much, horn players and singers are influences, and really, most of all, bands. It's not such much what Miles Davis is doing in his classic quintets, it's what all five of them are doing—and ditto for the John Coltrane Quartet. The collective, intuitive dance between several musicians is a big part of what makes jazz jazz for me."

In the course of that exploration, Mehldau began experimenting with his approach, not only bringing in his interest in classical music (with his 1999 solo album Elegiac Cycle) but also modern influences such as drum 'n' bass grooves in his 2002 breakthrough Largo, which also managed to combine rock musicians, classical instruments, electronics, and prepared piano, yet remained a cohesive expression of his growing abilities. Since then, Mehldau has been prolific and unpredictable, from his recordings (such as 2009's Highway Rider, which combined his trio with a 28-piece orchestra) to his performances (for instance, a piano concerto dubbed "The Brady Bunch Variations for Piano and Orchestra" with the Orchestre national d'Île-de-France). His achievements are literally too numerous to list here.

Does he ever hesitate over whether he might be losing his longtime fans with right-angle shifts in direction and sound? Not at all.

"I'm really appreciative if someone takes the time to engage in a new project of mine, and if they have an aversion toward it, that's just fine—I get it," Mehldau says. "It's often the case with me as a fan. How could it be otherwise? We define what we believe in at least partially in terms of what we don't believe in as listeners—the two poles are interdependent."

One might be tempted to attribute Mehldau's cross-genre success to how audiences today listen to music. The rise of online music, particularly with streaming services, allows users to more easily ignore labels and listen to new sounds without preconceived notions. Or maybe it's social media, with friends directing friends to new things by the minute. But for Mehldau, this online terrain may have fewer barriers but it is also treacherous.

"It's hard for me to give a plug to online proliferation of music without qualifying it a lot," he says. "The music services provide as of yet a laughably paltry royalty rate for the musicians and composers, in the context of a market that is shrinking to nothingness because of a vague ethos of ‘information should be free.' That is really just ignorance: Ignorance of the very real cost in time, dedication, and craft that is required from the artists—who absolutely should be compensated by anyone who enjoys the music.

"Having said that, the great part of the Web more generally that I have observed is it potentially breaks down useless categories of music which are only nominal and may limit people's exposure. And that's great for jazz because a younger person may make his or her way to it all the more quickly. I say potentially because, in the online music services, and more insidiously, in the social media format, the listener is still viewed as a consumer, which means finding out ‘likes,' ‘dislikes,' and all that limiting baloney."